Search Cheap Flights to
Chester

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Chester Flights as Low as $74

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Thu, May 29 - Sat, May 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$74 Roundtrip, found 1 day ago
$74
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, May 29 from Orlando Intl. to Bradley Intl., returning Sat, May 31, priced at $74 found 1 day ago
Frontier Airlines
Thu, May 29 - Mon, Jun 2
MCO
Orlando Intl.
BDL
Bradley Intl.
$80 Roundtrip, found 1 day ago
$80
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, May 29 from Orlando Intl. to Bradley Intl., returning Mon, Jun 2, priced at $80 found 1 day ago
Frontier Airlines
Thu, May 29 - Sun, Jun 1
MCO
Orlando Intl.
BDL
Bradley Intl.
$85 Roundtrip, found 1 day ago
$85
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, May 29 from Orlando Intl. to Bradley Intl., returning Sun, Jun 1, priced at $85 found 1 day ago
Frontier Airlines
Thu, May 15 - Mon, May 19
MCO
Orlando Intl.
BDL
Bradley Intl.
$88 Roundtrip, found 1 day ago
$88
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, May 15 from Orlando Intl. to Bradley Intl., returning Mon, May 19, priced at $88 found 1 day ago
Frontier Airlines
Thu, May 22 - Sat, May 24
MCO
Orlando Intl.
BDL
Bradley Intl.
$89 Roundtrip, found 9 hours ago
$89
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Thu, May 22 from Orlando Intl. to Bradley Intl., returning Sat, May 24, priced at $89 found 9 hours ago
Frontier Airlines
Thu, May 22 - Fri, May 30
MCO
Orlando Intl.
BDL
Bradley Intl.
$90 Roundtrip, found 9 hours ago
$90
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Thu, May 22 from Orlando Intl. to Bradley Intl., returning Fri, May 30, priced at $90 found 9 hours ago
Spirit Airlines
Fri, May 30 - Mon, Jun 2
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$98 Roundtrip, found 6 days ago
$98
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Fri, May 30 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Jun 2, priced at $98 found 6 days ago
Breeze Airways
Thu, May 15 - Mon, May 19
MCO
Orlando Intl.
BDL
Bradley Intl.
$125 Roundtrip, found 1 day ago
$125
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, May 15 from Orlando Intl. to Bradley Intl., returning Mon, May 19, priced at $125 found 1 day ago
Breeze Airways
Fri, Jul 11 - Mon, Jul 14
TPA
Tampa Intl.
BDL
Bradley Intl.
$126 Roundtrip, found 11 hours ago
$126
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Fri, Jul 11 from Tampa Intl. to Bradley Intl., returning Mon, Jul 14, priced at $126 found 11 hours ago
JetBlue Airways
Tue, Jun 10 - Tue, Jun 10
MCO
Orlando Intl.
BDL
Bradley Intl.
$144 Roundtrip, found 5 days ago
$144
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Tue, Jun 10 from Orlando Intl. to Bradley Intl., returning Tue, Jun 10, priced at $144 found 5 days ago
American Airlines
Tue, Aug 5 - Tue, Aug 12
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$151 Roundtrip, found 3 days ago
$151
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Aug 5 from Charlotte-Douglas Intl. to Bradley Intl., returning Tue, Aug 12, priced at $151 found 3 days ago
Delta
Tue, Aug 5 - Tue, Aug 12
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$197 Roundtrip, found 3 days ago
$197
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Aug 5 from Charlotte-Douglas Intl. to Bradley Intl., returning Tue, Aug 12, priced at $197 found 3 days ago
United
Fri, May 16 - Sun, May 18
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$206 Roundtrip, found 1 day ago
$206
Roundtrip
found 1 day ago
Select United flight, departing Fri, May 16 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Sun, May 18, priced at $206 found 1 day ago
Spirit Airlines
Sat, May 24 - Thu, May 29
IAH
George Bush Intercontinental
BDL
Bradley Intl.
$217 Roundtrip, found 5 days ago
$217
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Sat, May 24 from George Bush Intercontinental to Bradley Intl., returning Thu, May 29, priced at $217 found 5 days ago
Spirit Airlines
Wed, Jul 9 - Wed, Jul 16
DFW
Dallas-Fort Worth Intl.
BDL
Bradley Intl.
$226 Roundtrip, found 19 hours ago
$226
Roundtrip
found 19 hours ago
Select Spirit Airlines flight, departing Wed, Jul 9 from Dallas-Fort Worth Intl. to Bradley Intl., returning Wed, Jul 16, priced at $226 found 19 hours ago
Delta
Tue, Sep 30 - Tue, Oct 7
DAL
Love Field
BDL
Bradley Intl.
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep 30 from Love Field to Bradley Intl., returning Tue, Oct 7, priced at $237 found 1 day ago

Cheap Flights to Chester

Fall in love at first flight with your vacation to Chester by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Chester on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Chester, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Chester

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Chester with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the CEF airport.

What is the cheapest month to fly to Chester?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Chester are in May, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Chester?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Chester.

What airport is best to fly into Chester?

When you’re planning your trip to Chester, convenience is the name of the game. Luckily, Chester Barnes Municipal Airport is nearby so you can deplane and get going on checking off everything on your Chester must-do list.

How much are flights to Chester?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Chester on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $74, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Chester?

The trick to saving a stack of cash on your flight to Chester? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $74 right now, why wait?

Last Minute Hotel Deals in Chester

D. Hotel Suites & Spa
D. Hotel Suites & Spa
3 out of 5
1 Country Club Rd, Holyoke, MA
Stay at this 3-star spa hotel in Holyoke. Enjoy a full-service spa, 2 restaurants, and room service. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (2,278 reviews)

Reviewed on May 5, 2025

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D. Hotel Suites & Spa
Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (583 reviews)
"Great, clean, and updated property. Excellent location."

Reviewed on May 9, 2025

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Life House Berkshires
La Quinta Inn & Suites by Wyndham Springfield MA
La Quinta Inn & Suites by Wyndham Springfield MA
3 out of 5
100 Congress Street, Springfield, MA
Book a stay at this family-friendly hotel in Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
8/10 Very Good! (1,281 reviews)
"👍"

Reviewed on May 4, 2025

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La Quinta Inn & Suites by Wyndham Springfield MA
Quality Inn West Springfield
Quality Inn West Springfield
2.5 out of 5
1150 Riverdale St, West Springfield, MA
Book a stay at this golf hotel in West Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
7/10 Good! (1,000 reviews)
"Solid for a night"

Reviewed on May 6, 2025

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Quality Inn West Springfield
The Ellery
The Ellery
3.5 out of 5
259 Elm Street, Northampton, MA
Stay at this 3.5-star B&B in Northampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9/10 Wonderful! (672 reviews)
Nice overnight stay
"Very easy to check in, polite staff. The room was large and very clean. The bathroom was updated (but the door didn't close properly). Overall it was a very comfortable stay. The included breakfast options were very good."

Reviewed on May 5, 2025

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The Ellery
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Black Swan Lee - Lenox, Ascend Hotel Collection
3 out of 5
435 Laurel St, Lee, MA
Stay at this 3-star hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular ...
9/10 Wonderful! (1,000 reviews)
"Pleasant stay. Great staff. Really good Indian restaurant in the hotel. Peaceful and relaxing"

Reviewed on May 6, 2025

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The Black Swan Lee - Lenox, Ascend Hotel Collection
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9/10 Wonderful! (1,001 reviews)
"I had a wonderful stay at The Yankee, Trademark Collection by Wyndham. The room was beautiful and comfortable, making for a very relaxing experience. The staff was incredibly kind, welcoming, and made check-in and check-out effortless. However, during my visit, there was construction happening nearby, ..."

Reviewed on May 7, 2025

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The Yankee, Trademark Collection by Wyndham
Quality Inn & Suites Northampton - Amherst
Quality Inn & Suites Northampton - Amherst
2.5 out of 5
117 Conz St, Northampton, MA
Book a stay at this business-friendly hotel in Northampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7/10 Good! (1,001 reviews)
"No problems, could have been a little cleaner in the bathroom but overall great"

Reviewed on May 3, 2025

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Quality Inn & Suites Northampton - Amherst
See all 823 properties in Chester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.